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Ring‐Cleavage Reactions of Five‐ and Six‐Membered Cyclic Ethers with Organolithium Compounds
Author(s) -
Chou TaShue,
Hung ShaoHwa,
Cheng ChienChung
Publication year - 1990
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199000087
Subject(s) - chemistry , boron trifluoride , tetrahydropyran , cleavage (geology) , regioselectivity , organolithium compounds , ring (chemistry) , organic chemistry , medicinal chemistry , catalysis , ion , geotechnical engineering , fracture (geology) , deprotonation , engineering
In the presence of one equivalent of boron trifluoride etherate, organolithium compounds cause the ring cleavage reactions of tetrahydrofurans and tetrahydropyran to give the corresponding long‐chain alcohols in moderate yields. These reactions are highly regioselective for unsymmetric cyclic ethers.